Trimethylsilyldiazomethane → Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate

HRID 1092064

Reaktionsgleichung

Reaktionsgleichung von HRID 1092064
[CH3:1][Si](C=[N+]=[N-])(C)C.[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH2:11][CH2:10]1>C1(C)C=CC=CC=1.CO.C(Cl)Cl>[CH3:8][N:9]1[CH2:10][CH2:11][N:12]([CH2:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([O:22][CH3:1])=[O:21])=[CH:18][CH:17]=2)[CH2:13][CH2:14]1

Komponenten

6

Edukt 2

HCID 167693Trimethylsilyldiazomethane2×HCID 47697824-(4-Methyl-1-piperazinylmethyl)benzoic acid

Produkt 1

HCID 782222Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoateAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of (trimethylsilyl)diazomethane ((0.611 mL, 3.84 mmol) 2.0M in diethyl ether) was added dropwise to a stirred suspension of 4-((4-methylpiperazin-1-yl)methyl)benzoic acid (0.75 g, 3.20 mmol) in toluene (21 mL) and methanol (7 mL) over a period of 10 mins under nitrogen. The resulting suspension was stirred at room temperature for 3 h. A further aliquot of (trimethylsilyl)diazomethane (1.222 mL, 7.68 mmol) was added dropwise and the solution was stirred at room temperature for a further 18 h. The reaction mixture was evaporated to dryness to afford the crude product (0.723 g) as a white solid. This was taken up in DCM and the insolubles were filtered off. The filtrate was evaporated to dryness to afford the crude product. This was taken up in DCM again and more insolubles were filtered off to afford methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate (0.351 g, 44.2%), which was used without purification.

Aufarbeitung

  1. stirringthe solution was stirred at room temperature for a further 18 h
  2. customThe reaction mixture was evaporated to dryness
  3. customto afford the crude product (0.723 g) as a white solid
  4. filtrationthe insolubles were filtered off
  5. customThe filtrate was evaporated to dryness
  6. customto afford the crude product
  7. filtrationmore insolubles were filtered off

Quellen und Nachweise

ORD-Eintrag
ord-4d95eaf64740474096573688ff61119a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129391B2

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